Norbornene in Organic Synthesis,Synthesis

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Norbornene in Organic Synthesis
Synthesis ( IF 2.6 ) Pub Date : 2018-06-25 , DOI: 10.1055/s-0037-1610143
Jianhui Huang _{1,

2,

3} , Caifeng Li _{1,

2,

3} , Liu Liu _{1,

2,

3} , Xuegang Fu _{1,

2,

3}

Affiliation

Dedicated to Prof. Kang Zhao on the occasion of his 60^th birthday

Abstract

The norbornene skeleton possesses an alkene functionality with a fixed conformation, and represents unique reactivity. The use of norbornene and analogues as substrates is overviewed; reactivities are discussed as well as the role of norbornenes as ligands assisting modern organic transformations.

1 Introduction

2 Synthesis of Substituted Norbornenes

2.1 Preparation of Functionalized Norbornenes by Deprotonation and Substitution Reactions

2.2 Preparation of Functionalized Norbornenes under Palladium-Catalyzed Reaction Conditions

2.3 Alkylation of Norbornene

2.4 Multistep Synthesis

3 Synthesis of Substituted Norbornanes

3.1 Three-Membered-Ring Formation

3.2 Formation of Four-Membered Rings

3.3 Five- and Six-Membered Ring Formation

3.4 Syntheses of Difunctionalized Norbornanes

4 Synthesis of Cyclopentanes

4.1 Oxidation Reactions

4.2 Ring-Opening Cross Metathesis (ROCM)

4.3 Ring-Opening Metathesis Polymerization (ROMP)

4.4 Palladium-Catalyzed Ring-Opening of Norbornene

5 Norbornene-Mediated Reactions

5.1 Palladium Insertion into Carbon–Halide Bonds

5.2 Palladium Insertion into N–H and C–H Bonds

5.3 Norbornene as Ligand in Mediated Reactions

6 Conclusion

1 Introduction

2 Synthesis of Substituted Norbornenes

2.1 Preparation of Functionalized Norbornenes by Deprotonation and Substitution Reactions

2.2 Preparation of Functionalized Norbornenes under Palladium-Catalyzed Reaction Conditions

2.3 Alkylation of Norbornene

2.4 Multistep Synthesis

3 Synthesis of Substituted Norbornanes

3.1 Three-Membered-Ring Formation

3.2 Formation of Four-Membered Rings

3.3 Five- and Six-Membered Ring Formation

3.4 Syntheses of Difunctionalized Norbornanes

4 Synthesis of Cyclopentanes

4.1 Oxidation Reactions

4.2 Ring-Opening Cross Metathesis (ROCM)

4.3 Ring-Opening Metathesis Polymerization (ROMP)

4.4 Palladium-Catalyzed Ring-Opening of Norbornene

5 Norbornene-Mediated Reactions

5.1 Palladium Insertion into Carbon–Halide Bonds

5.2 Palladium Insertion into N–H and C–H Bonds

5.3 Norbornene as Ligand in Mediated Reactions

6 Conclusion

中文翻译：

降冰片烯在有机合成中的应用

专用于康钊教授在他的60之际^个生日

抽象的

降冰片烯骨架具有具有固定构象的烯烃官能度，并且代表独特的反应性。概述了降冰片烯及其类似物作为底物的使用。讨论了反应性以及降冰片烯作为协助现代有机转化的配体的作用。

1引言

2取代的降冰片烯的合成

2.1通过去质子化和取代反应制备功能化降冰片烯

2.2钯催化反应条件下功能化降冰片烯的制备

2.3降冰片烯的烷基化

2.4多步合成

3取代降冰片烷的合成

3.1三元环编队

3.2四元环的形成

3.3五元环和六元环的形成

3.4双官能降冰片烷的合成

4环戊烷的合成

4.1氧化反应

4.2开环交叉复分解（ROCM）

4.3开环易位聚合（ROMP）

4.4降冰片烯的钯催化开环

5降冰片烯介导的反应

5.1钯插入卤化碳键中

5.2钯插入N–H和C–H键

5.3降冰片烯作为介导反应中的配体

六，结论

1引言